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I bought the B&W P5 when they were on sale on the Apple store and do not regret it. They sound amazing, look amazing, and so far have been very durable. One of my fave tech purchases ever.
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ghoppeMar 7 '11 at 4:07

I would through another set of headphones into the pix, the Bose Quiet Comfort 3 headphones. They are $349 at Amazon.
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john busteedMar 7 '11 at 14:45

They look great, but they are open-backed, so will leak a fair amount of sound.
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Jason SundramMar 7 '11 at 6:06

@Jason Actually it´s really not that much sound leaking out (unless you´re going to toast your eardrums) then ambient noise leaking in that could be a problem with them; but since you said "look good on a desk" I automatically assumed you´d use them at home where this probably wouldn´t be a problem. Maybe you´ll want to consider the AKG K 272 HD instead (I didn´t buy them only because my ears are quite big and they didn´t fit well): akg.com/personal/K%20272%20HD,pcp_id,165,pid,79,_psmand,1.html
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AsmusMar 7 '11 at 13:53

thanks. I'll actually be using them at work, so the attenuation of outside noise is definitely a feature for me. I have a pair of Sennheiser HD600 that I use at home. They have an open design, and I have definitely been told by other people that they can hear what I'm listening to. Maybe I should turn the volume down...
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Jason SundramMar 7 '11 at 15:25

I have been using these headphones for a few years now and they are excellent and very comfortable. With the noise canceling engaged and some quiet music playing, almost all outside noise goes away completely. They are comfortable enough that I can wear them for several hours and feel no discomfort. They cost about $300. The only negative is that in order to play music, you must have the noise canceling feature turned on which requires a battery. So if you happen to be on the road (say, in an airplane) and your battery dies, you are SOL. So definitely make sure you have a spare charged AAA battery nearby.

Aesthetic looks were never that important to me, but from comparing the other products you list, the Bose headset looks very similar so it should satisfy you in that department.

I've read some reviews on Amazon that suggest these break easily, and that Bose isn't great about fixing them under warranty. Do they feel durable and solid to you?
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Jason SundramMar 7 '11 at 16:06

@Jason Sundram I've broken a set. It was after several years of use and obviously after the warranty was up. It was my fault. I had the head phones buried in a backpack and I yanked them up by one ear and of course the other ear caught on something and I snapped it right off at the swivel hinge. I contacted Bose and I was able to replace them at a slight discount by shipping them my broken ones. So I am on pair number 2 in about 6 years. I am more careful when I travel with them now. I think they are relatively sturdy so long as you don't abuse them and you use the included case if you travel.
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sorensMar 7 '11 at 21:33

update: I just noticed that the padding around the earphones has started wear and degrade. This hasn't impacted me yet. My set is a few years old at this point, but it still seems that the material is degrading faster than I would like.
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sorensMar 9 '11 at 19:50

For casual listening you just can't beat the comfort and sound from a pair of Grado headphones. At your budget the SR325iare a great choice. They are open air so some sound will be heard in the vicinity near you, but they're not that loud to others around you.